7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

• ChemBase ID: 179763
• Molecular Formular: C13H16N2O
• Molecular Mass: 216.27894
• Monoisotopic Mass: 216.12626314
• SMILES: c12[nH]c3c(c1CCNC2C)ccc(c3)OC
• Canonical SMILES: COc1ccc2c(c1)[nH]c1c2CCNC1C
• InChI: InChI=1S/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3
• InChIKey: ZXLDQJLIBNPEFJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• IUPAC Traditional name: 7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• Synonyms: 2,3,4,9-Tetrahydro-7-methoxy-1-methyl-1H-pyrido[3,4-b]indole; 1,2,3,4-Tetrahydro-7-methoxy-1-methyl-beta-carboline; Leptaflorine; Tetrahydroharmine

Database IDs

• CAS Number: 17019-01-1
• PubChem SID: 164235673
• PubChem CID: 159809

CALCULATED PROPERTIES

• Acid pKa: 16.304031
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.2368844
• LogD (pH = 7.4): 0.1471129
• Log P: 1.8491501
• Molar Refractivity: 64.4616 cm^3
• Polarizability: 26.172483 Å^3
• Polar Surface Area: 37.05 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: 5HT serotonin inhibitor; MAO inhibitor

Product Information

• Biological Source: Alkaloid from Banisteriopsis caapi, Banisteriopsis argentea, Banisteriopsis inebrians, Leptactina densiflora, Peganum harmala and snuff used by South American Indians (Malphigiaceae, Rubiaceae, Zygophyllaceae).
• Application(s): Anthelmintic; Antiparkinsolic; Central nervous system stimulator; Coccidiostatic; Hallucinogen

REFERENCES

• Perkin, W.H. et al., J.C.S., 1919, 115, 961, (synth)
• Paris, R.R. et al., Bull. Soc. Chim. Fr., 1957, 780, (isol, struct, uv, ir)
• Hochstein, F.A. et al., J.A.C.S., 1957, 79, 5735, (isol)
• Bernauer, K., Helv. Chim. Acta, 1964, 47, 1075, (isol)
• Koblicova, Z. et al., Chem. Ind. (London), 1966, 1342, (abs config)
• Ghosal, S., Planta Med., 1972, 21, 200, (cmr)
• Chrisey, L.A. et al., Heterocycles, 1990, 30, 267, (resoln)